Adducts of monoepoxides and selected diamines

Abstract

The adducts of monoepoxides with selected diamines, preferably m-xylylenediamine, are useful as curing agents for the curing of epoxy resin compositions at very low temperatures (25 DEG -50 DEG F., -4 DEG to 10 DEG C.).

What is claimed is: 
     
       1. An adduct which is the reaction product of a monoepoxide selected from the group consisting of the alkyl glycidyl ethers where alkyl is of 3 to 14 carbon atoms, allyl glycidyl ether, phenyl glycidyl ether, the alkylphenyl glycidyl ethers where alkyl is of 1 to 18 carbon atoms and the glycidyl esters of the tertiary monocarboxylic acids of 9 to 11 carbon atoms, and a diamine selected from the group consisting of m-xylylenediamine, 1,2-diaminocyclohexane, isophoronediamine, 1,3-bis(aminomethyl)cyclohexane, 4,4'-diaminodiphenylmethane and 4,4'-diaminodicyclohexylmethane,   where the amount of monoepoxide used is 0.5 to 1.25 moles per each mole of diamine.   
     
     
       2. An adduct according to claim 1 where the monoepoxide is an alkyl glycidyl ether where alkyl is of 3 to 8 carbon atoms or is an alkylphenyl glycidyl ether where alkyl is of 1 to 4 carbon atoms. 
     
     
       3. An adduct according to claim 2 where the monoepoxide is butyl glycidyl ether or p-tert-butylphenyl glycidyl ether. 
     
     
       4. An adduct according to claim 1 where the diamine is m-xylylenediamine. 
     
     
       5. An adduct according to claim 1 wherein the monoepoxide is butyl glycidyl ether or p-tert-butylphenyl glycidyl ether and the diamine is m-xylylenediamine. 
     
     
       6. An adduct according to claim 1 wherein the amount of monoepoxide used is 0.85 to 1 mole per each mole of diamine. 
     
     
       7. An epoxy resin composition, curable at a temperature of 25°-50° F. (-4° to 10° C.), which comprises (a) an epoxy resin,   (b) an effective amount of an adduct prepared which is the reaction product of   a monoepoxide selected from the group consisting of the alkyl glycidyl ethers where alkyl is of 3 to 14 carbon atoms, allyl glycidyl ether, phenyl glycidyl ether, the alkylphenyl glycidyl ethers where alkyl is of 1 to 18 carbon atoms and the glycidyl esters of the tertiary monocarboxylic acids of 9 to 11 carbon atoms, and   a diamine selected from the group consisting of m-xylylenediamine, 1,2-diaminocyclohexane, isophoronediamine, 1,3-bis(aminomethyl)cyclohexane, 4,4'-diaminodiphenylmethane and 4,4'-diaminodicyclohexylmethane, where the amount of monoepoxide used is 0.5 to 1.25 moles per each mole of diamine,   (c) an effective amount of an accelerator, and   (d) an effective amount of a compatibilizing agent.   
     
     
       8. A composition according to claim 7 where the epoxy resin of component (a) is a liquid diglycidyl ether of bisphenol A. 
     
     
       9. A composition according to claim 7 wherein the adduct of component (b) is prepared from a monoepoxide which is an alkyl glycidyl ether where alkyl is of 3 to 8 carbon atoms or is an alkylphenyl glycidyl ether where alkyl is of 1 to 4 carbon atoms. 
     
     
       10. A composition according to claim 9 wherein the monoepoxide is butyl glycidyl ether or p-tertbutylphenyl glycidyl ether. 
     
     
       11. A composition according to claim 7 wherein the adduct of component (b) is prepared from a diamine which is m-xylylenediamine. 
     
     
       12. A composition according to claim 7 wherein the adduct of component (b) is prepared from a monoepoxide which is butyl glycidyl ether or p-tertbutylphenyl glycidyl ether and the diamine is m-xylylenediamine. 
     
     
       13. A composition according to claim 7 wherein the adduct of component (b) is prepared from 0.85 to 1 mole of monoepoxide per each mole of diamine. 
     
     
       14. A composition according to claim 7 wherein the accelerator of component (c) is selected from the group consisting of salicyclic acid, phenol, phenol substituted by alkyl of 1 to 12 carbon atoms and the Mannich bases prepared from the reaction of phenol, formaldehyde and the dialkylamines. 
     
     
       15. A composition according to claim 14 wherein the accelerator is salicylic acid. 
     
     
       16. A composition according to claim 7 wherein the compatibilizing agent of component (d) is selected from the group consisting of benzyl alcohol, diethylene glycol, dipropylene glycol, the lower alkyl monoethers of ethylene glycol and the lower alkyl monoethers of propylene glycol. 
     
     
       17. A composition according to claim 16 wherein the compatibilizing agent is benzyl alcohol.